Citric Acid → HCID 22350974, compound

HRID 747519Notes

Reaction equation

HRID 747519 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[N:13]([CH2:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][OH:20])[C:12]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH:11][S:10]2)=[C:4]([O:28][CH3:29])[CH:3]=1.[OH-:30].[Na+].O.C(O)(=O)[CH2:34][C:35]([CH2:40]C(O)=O)([C:37](O)=O)[OH:36].[CH2:46]([OH:48])C>>[C:35]([O:36][C:46]([N:17]([CH2:16][CH2:15][CH2:14][N:13]1[C:12]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[CH:11][S:10][C:9]1=[N:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[O:28][CH3:29])[CH2:18][C:19]([OH:30])=[O:20])=[O:48])([CH3:34])([CH3:37])[CH3:40]

Participants

6

Reactant 5

HCID 311Citric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 22350987HCID 22350987, compound

Product 1

HCID 22350974HCID 22350974, compound

Procedure

To a solution of the compound (3 g) obtained in Example 321 (1) in ethanol (5 ml) was added dropwise a 4N aqueous sodium hydroxide solution (5 ml), and the mixture was stirred at room temperature for 4 hours. To the reaction mixture was added water, and the mixture was acidified with a 10% aqueous citric acid solution, and extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (2.92 g) as foam.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2b758480b96d4f3493c1884ba108ab68
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

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